Windward Village Vacation Rentals

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Vacation rentals in Windward Village feature comfortable villa-style accommodations with open living areas, private patios or balconies, and peaceful landscaped surroundings. Many units overlook lagoons or wooded areas, creating a quiet setting while remaining just a short walk or bike ride from Shipyard’s private beach access.

Guests staying in Windward Village enjoy access to Shipyard Plantation amenities, including miles of leisure trails, championship golf courses, tennis facilities, and beach access points. The community is conveniently located near Coligny Plaza, Forest Beach, and Sea Pines, placing shopping, dining, entertainment, and grocery stores just minutes away.

Choosing a Windward Village vacation rental in Shipyard Plantation delivers the ideal blend of comfort, convenience, and island charm. Whether you’re planning a family beach vacation, a golf getaway, or an extended stay, Windward Village provides a welcoming Hilton Head experience in one of the island’s most desirable gated communities.

Properties Available 7 properties available
Welcome to number 2 Sailmaster Common Shipyard Resort on beautiful Hilton Head Island! This townhouse is a secluded gem, offering a comfortable stay for our guests. Situated just a little over a mile away from the Shipyard Beach Club, you\'ll have quick and easy access to the pristine sandy shores and sparkling blue waters Hilton Head Island i
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Sailmaster 2
Shipyard
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
This two-story townhouse has been beautifully updated and is located within the gated community of Shipyard Resort, perfect for both beach and golf enthusiasts. With 3 bedrooms and 3.5 baths, this townhouse is ideal for families and groups of friends. The slightly elevated first floor features a spacious living room and flat screen TV. A half bath
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Beachwalk 145
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Beachwalk 145
Shipyard
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
Welcome to The Greens! Your vacation will be special in this 1 bedroom, 1.5 bath townhouse style villa within the gated community of Shipyard Resort, perfect for both beach and golf enthusiasts. Upon entering The Greens 168 you will find a spacious open floor plan. To the right of the entrance is the dining area with seating for four, next to the
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Greens 168
Shipyard
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
Welcome to 146 Windward Village in Shipyard Resort on beautiful Hilton Head Island! This elevated townhouse is a secluded gem, offering a comfortable stay for our guests. Situated just 2 miles away from the Shipyard Beach Club, you\'ll have quick and easy access to the pristine sandy shores and sparkling blue waters Hilton Head Island is known
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Windward Village 146
Shipyard
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
This villa is a beautifully renovated and welcoming 2 bedroom, 2 bath, second floor, bright, end unit with lagoon and pool views. It\'s the perfect place to stay for your Hilton Head Island getaway! The Colonnade Club complex is located within the gated community of the Shipyard Resort and is close to the beach. This villa is located directly acr
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Colonnade Club 174
Shipyard
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 (21)
Colonnade Club 205 offers the convenience of a first-floor flat for guests to enjoy. The furnished villa is located in close proximity to the shared outdoor grilling area, the on-site pool, and poolside spa. Access to the beach is a short walk away through the adjacent beach path that leads directly to the Shipyard Beach Club. The villa includes
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Colonnade Club 205
Shipyard
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.6 (6)
This two-story townhouse has been beautifully updated and is located within the gated community of Shipyard Resort, perfect for both beach and golf enthusiasts. With 3 bedrooms and 3.5 baths, this townhouse is ideal for families and groups of friends. The first floor features a spacious living room with a sleeper sofa and flat screen TV. A half ba
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Beachwalk 153
Shipyard
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (25)

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